Trimethyl phosphite → Dimethyl 1-eicosanyloxycarbonylphosphonate

HRID 2119772Notes

Reaction equation

HRID 2119772 reaction equation
Cl[C:2]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[O:3].[P:25]([O:30]C)([O:28][CH3:29])[O:26][CH3:27]>>[CH2:5]([O:4][C:2]([P:25](=[O:30])([O:28][CH3:29])[O:26][CH3:27])=[O:3])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

3

Reactant 2

HCID 8472Trimethyl phosphiteHCID 10689919HCID 10689919, compound

Product 1

HCID 10646503Dimethyl 1-eicosanyloxycarbonylphosphonateYield 97%

Procedure

1-Eicosanyl chloroformate (6.0 g, 16.6 mmol) was added slowly to refluxing P(OMe)3 30 (mL), and after 2 hours the mixture was left at room temperature overnight. Excess P(OMe)3 was removed by vacuum distillation, and the remaining white solid was collected, washed with cold hexane, and recrystallized from hexane to obtain colorless crystals from which traces of hexane were not fully removed (7.0 g, 97% yield); mp 53-54° C.; TLC: Rf 0.39 (silica gel, 98:2 CHCl3—MeOH); IR (KBr): υ 2950, 2915, 1705, 1540, 1280, 1220 cm−1; 1H NMR (CDCl3) δ0.8-1.8 (m, >39H, CH3(CH2)18), 3.9 (d, 6H, P(OCH3)2), 4.3 (t, 2H, CH2O). Anal. Calcd. for C23H47O5P.0.15C6H14: C, 64.13, H, 11.08; P, 6.92. Found: C, 63.91; H, 10.91; P, 6.62.

Workup

  1. customExcess P(OMe)3 was removed by vacuum distillation
  2. customthe remaining white solid was collected
  3. washwashed with cold hexane
  4. customrecrystallized from hexane
  5. customto obtain colorless crystals from which traces of hexane
  6. customwere not fully removed (7.0 g, 97% yield)

Sources & evidence

ORD record
ord-24c936b015fd4d3bb261f3adc54b1a04
Source dataset
uspto-grants-2004_02
Patent number
US06686462B2

Reaction notes

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